We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Airbnb your place

Holiday rentals in Lakeland-Winter Haven Metropolitan Area

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Lakeland-Winter Haven Metropolitan Area

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Guest house in Lakeland

4.88 out of 5 average rating, 140 reviews

Cozy studio In Historic Lake Morton district

This cozy, Ground level studio is on our homes property, it has a KITCHENETTE, WITH LIMITED COOKING. It is nestled in the Historic District of Lakeland and mere steps from Florida Southern a Frank Lloyd Wright designed campus, a tour is recommended! Our cobblestone streets take you to unique neighborhood restaurants. We are walking distance of beautiful downtown Lakeland. We are between two lakes- Lake Hollingsworth, a great 3+ mile walking/running path and Lake Morton which is a bird paradise.

29 Jun – 6 Jul

$60 SGD per night

Guest favourite

Townhouse in Lakeland

4.97 out of 5 average rating, 179 reviews

Glam Townhouse in Downtown Lakeland - 2bed/2bath

Location, Comfort, and Privacy! We have all you look for one night or extended stay. This apartment was newly remodeled and designed for you to feel like home. Private garage, lock code system (key-less). Walking distance from Lake Hollingsworth, Morton, local coffee shops, restaurants, gas stations, etc. Lakeland is also conveniently located between Orlando and Tampa. 40minutes from Disney & Bush Gardens, 30min to Legoland, 1 hour from Orlando/Universal, and the gorgeous beaches on the gulf.

24 Jun – 1 Jul

$181 SGD per night

Guest favourite

Guest house in Lakeland

4.96 out of 5 average rating, 141 reviews

Cozy Studio + Secluded Courtyard, SEU, FSC, dwntwn

Enjoy your stay in Lakeland in our cozy, newly remodeled studio! It is centrally located in Lakeland and a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) It comes fully equipped with everything you will need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the cozy modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Parking is just a few steps down the pathway through the courtyard from your door!

4–11 Oct

$143 SGD per night

Guest favourite

Home in Lakeland

4.96 out of 5 average rating, 113 reviews

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

6–13 Jul

$191 SGD per night

Guest favourite

Guest house in Lakeland

4.99 out of 5 average rating, 72 reviews

Serenity at Success

Located in the charming Lake Morton Historic District on Success Avenue . The completely detached suite is a two minute walk from Lake Morton & a half mile from Lake Hollingsworth which boasts a popular paved path, & one block away from FL Southern College. I’m a leisurely 1 mile walk to downtown Lakeland where you’ll find multiple bars, eating establishments, and shopping. I walk or bike 80% of the time to everything downtown. The famous swans of Lake Morton are less then a two minute walk.

31 May – 7 Jun

$173 SGD per night

Guest favourite

Home in Lakeland

4.9 out of 5 average rating, 41 reviews

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

18–25 Oct

$156 SGD per night

Guest favourite

Apartment in Lakeland

4.97 out of 5 average rating, 29 reviews

New! Charming Lakefront Condo

Enjoy an experience at this centrally-located place in the heart of Lakeland with a style all its own! Perfect for a stylish atmosphere for work or pleasure. Enjoy the neighborhood park, the wildlife of Lake Hunter, or take a walk to downtown Lakeland with it's many restaurants, entertainment, and more beautiful lakes. Across the street from Lake Hunter & only a mile from Lake Hollingsworth! Just 36 miles from Disney, 43 miles from Universal, & 17 miles from Legoland!

29 Aug – 5 Sep

$136 SGD per night

Guest favourite

Bungalow in Lakeland

4.99 out of 5 average rating, 97 reviews

Charming Bungalow with Front Porch

Enjoy peace and serenity at this centrally located, charming, 1920's bungalow in Lakeland. You will find the front porch an inviting spot to relax and unwind on this quiet street in the Lake Morton historical district. Downtown Lakeland, a Publix grocery store, Dixieland shopping, restaurants, bars and a liquor store are less than a five minute drive away. FSC, Lake Morton and Lake Hollingsworth with its 3 mile, paved walking trail are within a few, walkable blocks.

7–14 Jul

$154 SGD per night

Guest favourite

Guest house in Lakeland

4.95 out of 5 average rating, 101 reviews

Hidden Emerald-Apartment with Kitchen and Laundry

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between the major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, yard sitting area, washer & dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

4–11 Sep

$127 SGD per night

Guest favourite

Guest house in Lakeland

4.98 out of 5 average rating, 212 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

29 Jul – 5 Aug

$151 SGD per night

Guest favourite

Home in Lakeland

4.91 out of 5 average rating, 378 reviews

Charming guest house

PRIVATE 1 bedroom 1 bath guest house! NO SHARED SPACES. Private patio with HOT TUB all to yourself during your stay! We’re centrally located in Lakeland between Tampa and Orlando. We’re on a nice quiet 1 acre property out in the country but still within 10 minutes of the mall, local parks, stores, and all major restaurants.

17–24 Sep

$131 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Lakeland-Winter Haven Metropolitan Area

Guest favourite

Flat in Lakeland

5.0 out of 5 average rating, 59 reviews

Lakefront Property with Swans – Walk to Downtown

21–28 Jul

$154 SGD per night

Guest favourite

Guest house in Lakeland

4.9 out of 5 average rating, 30 reviews

Guest Home, Downtown, Lk Morton, FL Southern

4–11 Mar

$133 SGD per night

Guest favourite

Guest house in Lakeland

4.94 out of 5 average rating, 81 reviews

Beacon Hill Historic District - Cozy Cottage

19–26 May

$148 SGD per night

Guest favourite

Home in Lakeland

4.88 out of 5 average rating, 60 reviews

Charming and comfy apt near downtown

26 Oct – 2 Nov

$131 SGD per night

Guest favourite

Home in Lakeland

4.97 out of 5 average rating, 76 reviews

Cozy Lake House Retreat - Amazing Views !

26 Nov – 3 Dec

$202 SGD per night

Guest favourite

Home in Lakeland

4.99 out of 5 average rating, 94 reviews

Swan Studio Lakeland

5–12 Jun

$133 SGD per night

Guest favourite

Flat in Lakeland

5.0 out of 5 average rating, 15 reviews

The Suite Spot @ Lake Hollingsworth

7–14 Jun

$156 SGD per night

Guest favourite

Home in Lakeland

4.93 out of 5 average rating, 61 reviews

Queen's Suite with King Bed

22–29 Jul

$117 SGD per night

Destinations to explore